Carbon Disulfide → HCID 14951343, compound

HRID 2211176Notes

Reaction equation

HRID 2211176 reaction equation
[OH-].[K+].[F:3][C:4]([F:23])([F:22])[C:5]1[CH:6]=[C:7]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([NH:16][NH2:17])=[O:15])[CH:8]=[CH:9][CH:10]=1.[C:24](=S)=[S:25]>CO>[F:3][C:4]([F:22])([F:23])[C:5]1[CH:6]=[C:7]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]2[O:15][C:24](=[S:25])[NH:17][N:16]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 131678272-[(3-Trifluoromethylphenyl)amino]benzoic acid hydrazide

Product 1

HCID 14951343HCID 14951343, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (123.0 mg, 1.87 mmol) is added to a 020 C. solution of 2-[(3-trifluoromethylphenyl)amino]-benzoic acid, hydrazide (515.8 mg, 1.75 mmol) and carbon disulfide (250 μl, 3.96 mmol) in 15 ml of methanol. The mixture is heated at reflux overnight. The solution is concentrated in vacuo and the residue dissolved in water. The resulting aqueous solution is acidified with 1N hydrochloric acid and the resulting solids extracted into a 1:1 mixture of ether and ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is chromatographed, eluting with hexane:ethyl acetate (1:1), providing a white solid. Drying in vacuo at 65° C. overnight gives 406.4 mg (69%) of product, mp 211°-213° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight
  3. concentrationThe solution is concentrated in vacuo
  4. dissolutionthe residue dissolved in water
  5. extractionthe resulting solids extracted into a 1:1 mixture of ether and ethyl acetate
  6. washThe organic layer is washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is chromatographed
  11. washeluting with hexane:ethyl acetate (1:1)
  12. customproviding a white solid
  13. customDrying in vacuo at 65° C. overnight

Sources & evidence

ORD record
ord-cd7b3a4aec4c4231b9c5602912550119
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

Loading…